(3S,4R,E)-4-(tert-butyldimethylsilyloxy)-1-((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3, 4-d][1,3]dioxol-4-yl)pent-1-en-3-yl benzoate

Base Information

Chemical Name:(3S,4R,E)-4-(tert-butyldimethylsilyloxy)-1-((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3, 4-d][1,3]dioxol-4-yl)pent-1-en-3-yl benzoate
CAS No.:1403891-26-8
Molecular Formula:C₃₀H₄₆O₈Si
Molecular Weight:562.776
Hs Code.:

(3S,4R,E)-4-(tert-butyldimethylsilyloxy)-1-((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3, 4-d][1,3]dioxol-4-yl)pent-1-en-3-yl benzoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4R,E)-4-(tert-butyldimethylsilyloxy)-1-((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3, 4-d][1,3]dioxol-4-yl)pent-1-en-3-yl benzoate

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Technology Process of (3S,4R,E)-4-(tert-butyldimethylsilyloxy)-1-((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3, 4-d][1,3]dioxol-4-yl)pent-1-en-3-yl benzoate

There total 2 articles about (3S,4R,E)-4-(tert-butyldimethylsilyloxy)-1-((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3, 4-d][1,3]dioxol-4-yl)pent-1-en-3-yl benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1403891-24-6
(3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[3,4-d][1,3]dioxole

: 1403891-25-7
(3S,4R)-4-(tert-butyldimethylsilyloxy)pent-1-en-3-yl benzoate

: (3S,4R,Z)-4-(tert-butyldimethylsilyloxy)-1-((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3, 4-d][1,3]dioxol-4-yl)pent-1-en-3-yl benzoate

: 1403891-26-8
(3S,4R,E)-4-(tert-butyldimethylsilyloxy)-1-((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3, 4-d][1,3]dioxol-4-yl)pent-1-en-3-yl benzoate

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; for 12h; Overall yield = 67 %; Overall yield = 339 mg;
DOI:10.1021/jo301829p

Reference yield:

: 852612-81-8
C₁₄H₂₄O₆

: (3S,4R,Z)-4-(tert-butyldimethylsilyloxy)-1-((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3, 4-d][1,3]dioxol-4-yl)pent-1-en-3-yl benzoate

: 1403891-26-8
(3S,4R,E)-4-(tert-butyldimethylsilyloxy)-1-((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3, 4-d][1,3]dioxol-4-yl)pent-1-en-3-yl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine; p-toluenesulfonyl chloride / 65 °C / Inert atmosphere

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / 20 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; p-toluenesulfonyl chloride; In dichloromethane;
DOI:10.1021/jo301829p